Preparation and antimicrobial activity of some carboxymethyl chitosan acyl thiourea derivatives

Int J Biol Macromol. 2012 Jun 1;50(5):1280-5. doi: 10.1016/j.ijbiomac.2012.03.011. Epub 2012 Mar 26.

Abstract

Acetyl, chloroacetyl and benzoyl thiourea derivatives of carboxymethyl chitosan (ATUCMCS, CATUCMCS, and BZTUCMCS) with comparable grafting degree were synthesized and their structures were characterized by FTIR spectroscopy and elemental analyses. The antimicrobial behaviors of CMCS and its derivatives against three types of bacteria [Bacillis subtilis (B. subtilis), Staphylococous aureus (S. aureus) and Escherichia coli (E. coli)] and three crop-threatening pathogenic fungi [Aspergillus fumigate (A. fumigate), Geotrichum candidum (G. candidum) and Candida albicans (C. albicans)] were investigated. The results indicated that the antibacterial and the antifungal activities of the acyl thiourea derivatives are much higher than that of the parent CMCS. The acyl thiourea derivatives were more potent in case of Gram-positive bacteria than Gram-negative bacteria. This is illustrated for example by the values of minimum inhibitory concentration (MIC) of the ATUCMCS, CATUCMCS and BZTUCMCS against B. subtilis were 3.9, 15.6 and 62.5, respectively, while the MIC values of these derivatives against E. coli were 62.5, 125 and 500. Moreover, the antifungal activity of the CATUCMCS is higher than that of the acetyl and benzoyl thiourea derivatives. This may be due to the presence of chlorine atom.

MeSH terms

  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology*
  • Bacteria / drug effects
  • Chitosan / analogs & derivatives*
  • Chitosan / chemistry
  • Chitosan / pharmacology
  • Fungi / drug effects
  • Microbial Sensitivity Tests
  • Thiourea / chemistry*

Substances

  • Anti-Infective Agents
  • carboxymethyl-chitosan
  • Chitosan
  • Thiourea